JP4497724B2 - 酢酸の微生物的製造方法ならびに醗酵ブロスからの酢酸の抽出のための溶媒 - Google Patents
酢酸の微生物的製造方法ならびに醗酵ブロスからの酢酸の抽出のための溶媒 Download PDFInfo
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- JP4497724B2 JP4497724B2 JP2000568812A JP2000568812A JP4497724B2 JP 4497724 B2 JP4497724 B2 JP 4497724B2 JP 2000568812 A JP2000568812 A JP 2000568812A JP 2000568812 A JP2000568812 A JP 2000568812A JP 4497724 B2 JP4497724 B2 JP 4497724B2
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- clostridium
- acetic acid
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- Expired - Fee Related
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 648
- 239000002904 solvent Substances 0.000 title claims description 383
- 238000000855 fermentation Methods 0.000 title claims description 96
- 230000004151 fermentation Effects 0.000 title claims description 95
- 238000000605 extraction Methods 0.000 title claims description 88
- 238000004519 manufacturing process Methods 0.000 title claims description 34
- 230000000813 microbial effect Effects 0.000 title description 14
- 238000000034 method Methods 0.000 claims description 158
- 239000006184 cosolvent Substances 0.000 claims description 152
- 239000000203 mixture Substances 0.000 claims description 134
- 238000004821 distillation Methods 0.000 claims description 109
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 106
- 239000007789 gas Substances 0.000 claims description 79
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 74
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 52
- 239000001569 carbon dioxide Substances 0.000 claims description 52
- 239000008346 aqueous phase Substances 0.000 claims description 46
- 235000015097 nutrients Nutrition 0.000 claims description 45
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 42
- 239000012071 phase Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 40
- 238000011084 recovery Methods 0.000 claims description 40
- 241000894006 Bacteria Species 0.000 claims description 38
- 238000009835 boiling Methods 0.000 claims description 38
- 125000005265 dialkylamine group Chemical group 0.000 claims description 38
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 37
- 230000008569 process Effects 0.000 claims description 36
- 241000193403 Clostridium Species 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 150000001412 amines Chemical class 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000002609 medium Substances 0.000 claims description 24
- 239000011877 solvent mixture Substances 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 21
- 125000005270 trialkylamine group Chemical group 0.000 claims description 21
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- 230000001580 bacterial effect Effects 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 244000005700 microbiome Species 0.000 claims description 17
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 16
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 16
- 238000000926 separation method Methods 0.000 claims description 16
- 238000005192 partition Methods 0.000 claims description 15
- 230000002829 reductive effect Effects 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 13
- 241000186566 Clostridium ljungdahlii Species 0.000 claims description 13
- 230000001965 increasing effect Effects 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 241000193401 Clostridium acetobutylicum Species 0.000 claims description 10
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 10
- 241000193448 Ruminiclostridium thermocellum Species 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 241000186570 Clostridium kluyveri Species 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 102100030787 ERI1 exoribonuclease 2 Human genes 0.000 claims description 7
- 101000938751 Homo sapiens ERI1 exoribonuclease 2 Proteins 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
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- 241001148471 unidentified anaerobic bacterium Species 0.000 claims description 7
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 6
- 241001468163 Acetobacterium woodii Species 0.000 claims description 5
- 241001464894 Blautia producta Species 0.000 claims description 5
- 241001656810 Clostridium aceticum Species 0.000 claims description 5
- 241000186398 Eubacterium limosum Species 0.000 claims description 5
- 241000193447 Thermoanaerobacter thermohydrosulfuricus Species 0.000 claims description 5
- 241000193446 Thermoanaerobacterium thermosaccharolyticum Species 0.000 claims description 5
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
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- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 241000186359 Mycobacterium Species 0.000 claims 8
- 241000589158 Agrobacterium Species 0.000 claims 4
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims 4
- 241000193161 Clostridium formicaceticum Species 0.000 claims 4
- 241000186394 Eubacterium Species 0.000 claims 4
- 241000191992 Peptostreptococcus Species 0.000 claims 4
- 241000235070 Saccharomyces Species 0.000 claims 4
- 229960001803 cetirizine Drugs 0.000 claims 4
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims 4
- 239000000428 dust Substances 0.000 claims 4
- 239000012046 mixed solvent Substances 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 229910002090 carbon oxide Inorganic materials 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 description 184
- 235000010633 broth Nutrition 0.000 description 52
- 239000002253 acid Substances 0.000 description 40
- YOFPVMWVLDSWKR-UHFFFAOYSA-N 11-methyl-n-(11-methyldodecyl)dodecan-1-amine Chemical compound CC(C)CCCCCCCCCCNCCCCCCCCCCC(C)C YOFPVMWVLDSWKR-UHFFFAOYSA-N 0.000 description 23
- 238000010640 amide synthesis reaction Methods 0.000 description 21
- 230000004048 modification Effects 0.000 description 19
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- 229910052717 sulfur Inorganic materials 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 238000010525 oxidative degradation reaction Methods 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- PZFYOFFTIYJCEW-UHFFFAOYSA-N n-tridecyltridecan-1-amine Chemical compound CCCCCCCCCCCCCNCCCCCCCCCCCCC PZFYOFFTIYJCEW-UHFFFAOYSA-N 0.000 description 3
- 238000004062 sedimentation Methods 0.000 description 3
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 230000000789 acetogenic effect Effects 0.000 description 2
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
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- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 2
- 229940094933 n-dodecane Drugs 0.000 description 2
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000193459 Moorella thermoacetica Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
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- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/54—Acetic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
- C07C211/07—Monoamines containing one, two or three alkyl groups, each having the same number of carbon atoms in excess of three
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Extraction Or Liquid Replacement (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9944098P | 1998-09-08 | 1998-09-08 | |
| US9943998P | 1998-09-08 | 1998-09-08 | |
| US9943898P | 1998-09-08 | 1998-09-08 | |
| US9947598P | 1998-09-08 | 1998-09-08 | |
| US60/099,475 | 1998-09-08 | ||
| US60/099,439 | 1998-09-08 | ||
| US60/099,438 | 1998-09-08 | ||
| US60/099,440 | 1998-09-08 | ||
| PCT/US1999/020416 WO2000014052A1 (en) | 1998-09-08 | 1999-09-07 | Microbial process for the preparation of acetic acid as well as solvent for its extraction from the fermentation broth |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002539759A JP2002539759A (ja) | 2002-11-26 |
| JP2002539759A5 JP2002539759A5 (cs) | 2007-01-25 |
| JP4497724B2 true JP4497724B2 (ja) | 2010-07-07 |
Family
ID=27493060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000568812A Expired - Fee Related JP4497724B2 (ja) | 1998-09-08 | 1999-09-07 | 酢酸の微生物的製造方法ならびに醗酵ブロスからの酢酸の抽出のための溶媒 |
Country Status (26)
| Country | Link |
|---|---|
| US (4) | USRE39175E1 (cs) |
| EP (2) | EP1112246B1 (cs) |
| JP (1) | JP4497724B2 (cs) |
| KR (2) | KR100632746B1 (cs) |
| CN (2) | CN1226273C (cs) |
| AR (1) | AR023046A1 (cs) |
| AT (1) | ATE286871T1 (cs) |
| AU (1) | AU760956C (cs) |
| BR (1) | BR9913527B1 (cs) |
| CA (2) | CA2686476A1 (cs) |
| CZ (2) | CZ302075B6 (cs) |
| DE (1) | DE69923192T2 (cs) |
| ES (1) | ES2237151T3 (cs) |
| HK (1) | HK1040981B (cs) |
| ID (1) | ID28710A (cs) |
| MY (1) | MY154362A (cs) |
| NO (2) | NO326769B1 (cs) |
| NZ (3) | NZ510200A (cs) |
| PL (2) | PL202725B1 (cs) |
| PT (1) | PT1112246E (cs) |
| RU (1) | RU2225445C2 (cs) |
| TR (4) | TR200809538T2 (cs) |
| TW (1) | TWI240717B (cs) |
| UA (1) | UA72220C2 (cs) |
| WO (1) | WO2000014052A1 (cs) |
| ZA (1) | ZA200101560B (cs) |
Families Citing this family (211)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4804599B2 (ja) | 1996-12-20 | 2011-11-02 | シーメンス・ウォーター・テクノロジーズ・コーポレイション | 洗浄方法 |
| UA72220C2 (uk) | 1998-09-08 | 2005-02-15 | Байоенджініерінг Рісорсиз, Інк. | Незмішувана з водою суміш розчинник/співрозчинник для екстрагування оцтової кислоти, спосіб одержання оцтової кислоти (варіанти), спосіб анаеробного мікробного бродіння для одержання оцтової кислоти (варіанти), модифікований розчинник та спосіб його одержання |
| US7074603B2 (en) | 1999-03-11 | 2006-07-11 | Zeachem, Inc. | Process for producing ethanol from corn dry milling |
| CN100575331C (zh) | 1999-03-11 | 2009-12-30 | 齐凯姆公司 | 一种生产乙醇的方法 |
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